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Merck
CN

SML0477

棘霉素

≥98% (HPLC), HIF-1α inhibitor, powder

别名:

N-(2-Quinoxalinylcarbonyl)-O-[N-(2-quinoxalinylcarbonyl)-D-seryl-L-alanyl-3-mercapto-N,S-dimethylcysteinyl-N-methyl-L-valyl]-D-seryl-L-alanyl-N-methylcysteinyl-N-methyl L-valine (81)-lactone cyclic (37)-thioester, Quinomycin A

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关于此项目

经验公式（希尔记法）:
C51H64N12O12S2
化学文摘社编号:
512-64-1
分子量:
1101.26
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
Storage condition:
desiccated

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产品名称

棘霉素, ≥98% (HPLC)

SMILES string

S1C(C2N(C(=O)C(NC(=O)C(COC(=O)C(N(C(=O)C(N(C(=O)C(NC(=O)C(COC(=O)C(N(C2=O)C)C(C)C)NC(=O)c5nc6c(nc5)cccc6)C)C)C1)C)C(C)C)NC(=O)c3nc4c(nc3)cccc4)C)C)SC

InChI

1S/C51H64N12O12S2/c1-25(2)38-49(72)74-22-36(59-42(65)34-21-53-30-17-13-15-19-32(30)57-34)44(67)55-28(6)46(69)63(10)40-48(71)62(9)39(26(3)4)50(73)75-23-35(58-41(64)33-20-52-29-16-12-14-18-31(29)56-33)43(66)54-27(5)45(68)60(7)37(47(70)61(38)8)24-77-51(40)76-11/h12-21,25-28,35-40,51H,22-24H2,1-11H3,(H,54,66)(H,55,67)(H,58,64)(H,59,65)

InChI key

AUJXLBOHYWTPFV-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

shipped in

dry ice

storage temp.

−20°C

Quality Level

100

相关类别

Application

Echinomycin has been used for inhibition of hypoxia-inducible factor 1.

Biochem/physiol Actions

Echinomycin is an antitumor antibiotic and potent hypoxia inducible factor 1α (HIF-1α) inhibitor.
Echinomycin is an antitumor antibiotic and potent hypoxia inducible factor 1α (HIF-1α) inhibitor. It binds to DNA via bifunctional intercalation, blocking the binding of HIF-1α, a transcription factor important in tumor growth. Echinomycin selectively eliminated cancer stem cells in a study with mouse lymphoma and human AML xenogeneic models, eradicating the lymphomas. Recently, echinomycin was also found to act as an antibiotic adjuvant having synergistic effects with novobiocin in gram negative bacteria.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Repr. 2

存储类别

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000482804
0000482806
0000482806
0000482804
0000437257

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Antitumour drug-DNA interactions: NMR studies of echinomycin and chromomycin complexes.
X L Gao et al.
Quarterly reviews of biophysics, 22(2), 93-138 (1989-05-01)
Hypoxia-inducible factor 1 mediates hypoxia-enhanced synthesis of progesterone during luteinization of granulosa cells
Yoshioka S, et al.
Journal of Reproduction and Development, 63, 75-85 (2017)
Jianqiu Zou et al.
Cell reports, 42(1), 112018-112018 (2023-01-21)
Cardiac maturation is crucial for postnatal cardiac development and is increasingly known to be regulated by a series of transcription factors. However, post-translational mechanisms regulating this process remain unclear. Here we report the indispensable role of neddylation in cardiac maturation.
Yongzhen Hu et al.
Molecular cancer therapeutics, 8(8), 2329-2338 (2009-08-13)
Abnormal activation of hypoxia-inducible factor-1 (HIF-1), one of the most important transcription factors for the adaptation of cells to hypoxia, is frequently observed in numerous types of solid tumors. Dysregulation of HIF-1 induces tumor angiogenesis and enhances the expression of
Dilip V Jarikote et al.
Bioorganic & medicinal chemistry, 19(2), 826-835 (2011-01-05)
Echinomycin is a natural depsipeptide, which is a bisintercalator, inserting quinoxaline units preferentially adjacent to CG base pairs of DNA. Herein the design and synthesis of echinomycin mimetics based on grafting of two quinoxaline residues onto a macrocyclic scaffold (glycophane)
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